• Korean Journal of Pharmacognosy
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• v.28 no.3
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• pp.112-116
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• 1997

Hibiscus syriacus L. (Malvaceae) is widely distributed over Korean, China, India and Siberia. The dried flower of Hibiscus syriacus is used as a folk medicine for curing of hematochezia, dysentery, obstruction due to wind-phlegm, regurgitation, and vomiting of food, and the dried root bark is used antipyretic, anthelmintic and antifungal agents. From a chloroform extract of root bark of this plant, compound I, II, and III were isolated and the structures were elucidated by various spectroscopic analyses. These compounds were identified as syringaresinol. E-N-feruloyltyramine, and Z-N-feruloyltyramine, respectively and were isolated from this plant for the first time. Compound II and III exhibited lipid peroxidation inhibitory activities with $IC_{50}$ of 15.5 and 28.6 ${\mu}g/ml$, respectively.

• Journal of Microbiology and Biotechnology
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• v.27 no.8
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• pp.1386-1391
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• 2017

The bioactivities of boxthron fruits, a source of oriental medicine, are well known, whereas phytochemical studies of the boxthorn stem are rare. In this study, the stem extract of boxthorn (Lycium chinense Miller) and its subfractions were evaluated for their effects on nitric oxide (NO) inhibition and procollagen type I peptide (PIP) synthesis. A phenolic amide isolated from the stem extract was also assayed for these effects. The compound, N-trans-feruloyltyramine, was identified by $^1H$, $^{13}C$, and 2D-nuclear magnetic resonance analyses. In NO inhibition, the chloroform fraction (CF) exhibited the strongest inhibitory activity ($MIC_{50}=24.69{\mu}g/ml$) among the subfractions of the ethanol extract (EE). N-trans-feruloyltyramine isolated from the CF showed strong NO inhibitory activity, presenting with an $MIC_{50}$ of $31.36{\mu}g/ml$. The EE, CF, and N-trans-feruloyltyramine shown to have NO inhibition activity were assayed for the activity of PIP synthesis. The EE and CF showed relatively high PIP values of 38.8% and 24.21% at $100{\mu}g/ml$, respectively. The PIP value for $20{\mu}g/ml$ N-trans-feruloyltyramine showed a 36% increase compared with the non-treated control, whereas that treated with $20{\mu}g/ml$ ascorbic acid as a positive control showed a 13% increase. The results suggest that the proper stem extract of boxthorn stem could be efficiently used to produce good cosmetic effects.

• Archives of Pharmacal Research
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• v.28 no.11
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• pp.1224-1227
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• 2005

Here we report the cytotoxic activity of three known compounds isolated for the first time from Corydalis pallida (Papaveraceae). An isoquinoline alkaloid, berberine, exhibited cytototoxic activity against two human cancer cell lines, HT-1080 (human fibrosarcoma) and SNU-638 (human stomach adenocarcinoma), with $IC_{50}$ values of 3.2 and 3.4 $\mu$g/mL, respectively. N­trans-feruloyltyramine and N-trans-feruloylmethoxytyramine were also isolated from this plant but were inactive.

• Korean Journal of Pharmacognosy
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• v.37 no.2 s.145
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• pp.97-102
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• 2006

Garlic(Allium sativum Linn) is widely used as a common condiment for a variety of foods and beverages. It has been well known that fresh garlic and garlic supplement of commercial preparations have various therapeutic properties including antimicrobial activity, antiplatelet aggregation, antihypertension, and cholesterol-lowering effects, which contribute to its increasing uses for an alternative medicine. Allicin(diallyl thiosulfinate), the major bioactive components of garlic, is formed by alliinase cleavage of the naturally occurring alliin upon crushing or mincing of garlic, and is the progenitor of a number of other products, such as diallyl disulfide. CYP3A4, heme-containing monooxygenase, is a key enzyme responsible for drug metabolism. Therefor, in the present study, we isolated and examined the compounds with CYP3A4-inhibiting activities from garlic. Among EtOAc extracts of garlic, we found that N-p-coumaroyltyramine and N-feruloyltyramine showed remarkable CYP3A4-inhibiting activities, compared to diallyl disulfide. Structures of the isolated active compounds were established by chemical and spectroscopic means.

• Bulletin of the Korean Chemical Society
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• v.33 no.4
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• pp.1253-1258
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• 2012

Two phenolic allopyranosides and two phenolic amide allopyranosides, along with eight known phenolic compounds, including cimicifugic acids, shomaside B, fukiic acid, isoferulic acid, and piscidic acid, were isolated from the n-butanolic extract of rhizomes of Cimicifuga heracleifolia. On-line spectroscopic data for UV, NMR, and MS from a combination of LC-NMR and LC-MS techniques directly and rapidly provided sufficient structural information to identify and confirm all the structures of major phenolic compounds in the extract, in addition to their HPLC profiles. This combined analytic information was then used as a dereplication tool for structure-guided screening in order to isolate unknown phenolic compounds in the extract. Successive fractionation and purification using semi-preparative HPLC acquired four unknown allopyranosides, and their structures were identified as cis-ferulic acid 4-O-${\beta}$-D-allopyranoside, trans-ferulic acid 4-O-${\beta}$-D-allopyranoside, trans-feruloyltyramine 4-O-${\beta}$-D-allopyranoside, and trans-feruloyl-(3-O-methyl)dopamine 4-O-${\beta}$-D-allopyranoside, based on a subsequent spectroscopic interpretation.

• Archives of Pharmacal Research
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• v.29 no.8
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• pp.627-632
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• 2006

Chromatographic separation of the MeOH extract from the stems and rhizomes of Sinomemium acutum led to the isolation of nine alkaloids and a lignan. Their structures were determined to be dauriporphine (1), bianfugecine (2), dauriporphinoline (3), menisporphine (4), (-)-syringaresinol (5), N-feruloyltyramine (6), acutumine (7), dauricumine (8), sinomenine (9), and magnoflorine (10) by spectroscopic means. These compounds were examined for their P-gp mediated MDR reversal activity in human cancer cells. Compound 1 showed the most potent P-gp MDR inhibition activity with an $ED_{50}$ value $0.03\;{\mu}g/mL$ and $0.00010\;{\mu}g/mL$ in the MESSA/DX5 and HCT15 cells, respectively.

• Archives of Pharmacal Research
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• v.26 no.8
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• pp.585-590
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• 2003

Activity-guided fractionation of the EtOAc-soluble extract of the whole plants of Sida acuta using a bioassay based on the induction of quinone reductase (OR) in cultured Hepa 1c1c7 mouse hepatoma cells, led to the isolation of ten active compounds of previously known structure, quindolinone (1), cryptolepinone (2), 11-methoxyquindoline (3), N-trans-feruloyltyramine (4), vomifoliol (5), loliolide (6), 4-ketopinoresinol (7), scopoletin (8), evofolin-A (9), and evofolin-B (10), along with five inactive compounds of known structure, ferulic acid, sinapic acid, syringic acid, ($\pm$)-syringaresinol, and vanillic acid. These isolates were identified by physical and spectral data measurement. A new derivative of quindolinone, 5,10-dimethylquindolin-11-one (1a) was synthesized and characterized spectroscopically. Of the active substances, compounds 1-3 and 1a exhibited the most potent QR activity, with observed CD (concentration required to double induction) values ranging from 0.01 to 0.12 $\mu$ g/mL. Six compounds were then evaluated in a mouse mammary organ culture assay, with cryptolepinone (2), N-trans-feruloyltyramine (4), and 5,10-dimethylquindolin-11-one (1a) found to exhibit 83.3, 75.0, and 66.7% inhibition of 7,12-dimethylbenz[a]anthracene-induced preneoplastic lesions, respectively, at a dose of 10 $\mu\textrm{g}$/mL.

• Journal of Applied Biological Chemistry
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• v.61 no.1
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• pp.39-46
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• 2018

Column chromatographic separation of the MeOH extract from the roots of Dicentra spectabilis yielded fourteen compounds, menisdaurin (1), menisdaurilide (2), trans-N-p-coumaroyltyramine (3), trans-N-p-feruloyltyramine (4), 4-O-feruloylquinicacid (5), chlorogenic acid (6), 3-O-feruloylquinicacid (7), ferulic acid (8), protopine (9), Kaempferol 3,7-di-O-${\beta}-{\text\tiny{D}}$-glucopyranoside (10), kaempferol 3-O-${\beta}-{\text\tiny{D}}$-glucopyranosyl-7-O-${\alpha}-{\text\tiny{L}}$-rhamnopyranoside (11), ${\alpha}-rhamnoisorobin$ (12), astragalin (13), and nicotiflorin (14). Their structures were determined on the basis of NMR spectroscopic data. Among them, compound 1, 3-8, and 10-14 isolated from this plant were reported for the first time. The isolated compounds (1-14) were tested for nitric oxide (NO) inhibitory activity on lipopolysaccharide-stimulated RAW 264.7 cells. Compound 3, 4 and 12 significantly inhibited NO production. Moreover, Compound 3 suppressed pro-inflammatory cytokines ($TNF-{\alpha}$, $IL-1{\beta}$ and IL-6) in a dose- dependent manner. These data suggest that compound 3 possess anti-inflammatory activity and might be useful natural materials for development of anti-inflammatory agent.

• Journal of Applied Biological Chemistry
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• v.58 no.3
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• pp.281-285
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• 2015

Human neutrophil elastase (HNE) represents a good therapeutic target for the treatment of inflammatory diseases as well as invasion of microorganism. The methanol extract of a aerial part of Chelidonium majus L. showed high activity against the neutrophil elastase with an $IC_{50}$ value of $100{\mu}g/mL$. Due to its potency, subsequent bioactivity-guided fractionation of methanol extract led to six alkaloids (1-6), which were identified as dihydrosanguinarine (1), (s)-stylopine (2), arnottianamide (3), (+)-chelidonine (4), spallidamine (5), and N-trans-feruloyltyramine (6). Among of them, three alkaloids (2, 5, and 6) inhibited HNE in a dose-dependent manner with $IC_{50}$ ranging between 11.6 and $51.0{\mu}M$. Lineweaver-Burk and Dixon plots, and their secondary replots showed that alkaloids (2, 5, and 6) were mixed inhibitors of HNE. The analysis of $K_I$ and $K_{IS}$ value proved that all inhibitors (2, 5, and 6) had reversible mixed type I mechanism.

• Nutrition Research and Practice
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• v.5 no.5
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• pp.412-420
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• 2011

The aim of the present study was to investigate the hypocholesterolemic effect and potential of tyramine derivatives from Lycii Cortex Radicis (LCR), the root bark of lycium (Lycium chenese Miller) in reducing lipid peroxidation. The activities of enzymes, hepatic 3-hydroxy 3-methylglutaryl (HMG) CoA reductase and acyl-CoA:cholesterol acyltransferase (ACAT) and LDL oxidation were measured in vitro and animal experiments were also performed by feeding LCR extracts to rats. The test compounds employed for in vitro study were trans-N-p-coumaroyltyramine (CT) and trans-N-feruloyltyramine (FT), LCR components, N-(p-coumaroyl)serotonin (CS) and N-feruloylserotonin (FS) from safflower seeds, ferulic acid (FA) and 10-gingerol. It was observed that FT and FS at the concentration of 1.2 mg/mL inhibited liver microsomal HMG CoA reductase activity by ~40%, but no inhibition of activity was seen in the cases of CT, CS, FA and 10-gingerol. Whereas, ACAT activity was inhibited ~50% by FT and CT, 34-43% by FS and CS and ~80% by 10-gingerol at the concentration of 1 mg/mL. A significant delay in LDL oxidation was induced by CT, FT, and 10-gingerol. For the animal experiment, five groups of Sprague-Dawley male rats were fed high fat diets containing no test material (HF-control), 1 and 2% of LCR ethanol extract (LCR1 and LCR2), and 1% of extracts from safflower seed (Sat) and ginger (Gin). The results indicated that total cholesterol level was significantly lower in Saf, LCR2 and Gin groups, and HDL cholesterol level was lower only in Gin group when compared with HF-control group; while there was no difference in the serum triglyceride levels among the five experimental groups. The level of liver cholesterol was significantly lower in LCR1 and LCR2 groups than HF-control Serum levels of TBARS were significantly lower only in LCR2 group when compared with HF-control group. From the observed results, we concluded that LCR can be utilized as a hypocholesterolemic ingredient in combination with ginger, especially for functional foods.